ABSTRACT
Crude enzymes were extracted from beef, pork and chicken and were employed to hydrolyze 1-palmitoyl-2-linoleoyl-phosphatidylcholine (PLPC) and oxidized PLPC, i.e. hydroperoxide of PLPC (PLPC-OOH) and hydroxide of PLPC (PLPC-OH). HPLC-ELSD and ESI-MS were used to characterize and determinate hydrolytic products. After hydrolysis at 37 °C for 180 min, 26.8 ~ 27.4%, 21.6 ~ 22.8% and 17.8 ~ 19.0% of substrates were hydrolyzed by crude enzymes from beef, pork and chicken, respectively. Phospholipase A2 (PLA2) was the major contributor to hydrolysis, which accounted for 47.8 ~ 49.6%, 45.8 ~ 48.7% and 46.6 ~ 46.8% of hydrolysis of PLPC, PLPC-OOH and PLPC-OH, respectively. Crude enzymes demonstrated almost same specificities towards PLPC, PLPC-OOH and PLPC-OH. Under actions of crude enzymes, hydroperoxyoctadecadienoic acids (HpODE) and hydroxyoctadecadienoic acids (HODE) were yielded as hydrolytic products of PLPC-OOH and PLPC-OH, respectively. These finding would be helpful to better understand the fate of hydroperoxides of phospholipids and formation of HODE during meat products manufacturing.
Subject(s)
Muscles/enzymology , Phosphatidylcholines/metabolism , Phospholipases A2/metabolism , Animals , Cattle , Chickens , Chromatography, High Pressure Liquid , Fatty Acids, Unsaturated/analysis , Fatty Acids, Unsaturated/metabolism , Hydrolysis , Phosphatidylcholines/chemistry , SwineABSTRACT
Novel phenoylated phosphatidylcholines were synthesized from 1,2-dipalmitoyl phosphatidylcholine/egg 1,2-diacyl phosphatidylcholine and phenolic acids such as ferulic, sinapic, vanillic and syringic acids. The structures of phenoylated phosphatidylcholines were confirmed by spectral analysis. 2-acyl-1-lyso phosphatidylcholine was synthesized from phosphatidylcholine via regioselective enzymatic hydrolysis and was reacted with hydroxyl protected phenolic acids to produce corresponding phenoylated phosphatidylcholines in 48-56% yields. Deprotection of protected phenoylated phosphatidylcholines resulted in phenoylated phosphatidylcholines in 87-94% yields. The prepared compounds were evaluated for their preliminary in vitro antimicrobial and antioxidant activities. Among the active derivatives, compound 1-(4-hydroxy-3,5-dimethoxy) cinnamoyl-2-acyl-sn-glycero-3-phosphocholine exhibited excellent antioxidant activity with EC50 value of 16.43µg/mL. Compounds 1-(4-hydroxy-3-methoxy) cinnamoyl-2-acyl-sn-glycero-3-phosphocholine and 1-(4-hydroxy-3,5-dimethoxy) cinnamoyl-2-palmitoyl-sn-glycero-3-phosphocholine exhibited good antioxidant activity with EC50 values of 36.05 and 33.35µg/mL respectively. Compound 1-(4-hydroxy-3-methoxy) cinnamoyl-2-palmitoyl-sn-glycero-3-phosphocholine exhibited good antibacterial activity against Klebsiella planticola with MIC of 15.6µg/mL and compound 1-(4-hydroxy-3-methoxy) benzoyl-2-acyl-sn-glycero-3-phosphocholine exhibited good antifungal activity against Candida albicans with MIC of 15.6µg/mL.
Subject(s)
Anti-Infective Agents/therapeutic use , Antioxidants/therapeutic use , Hydroxybenzoates/chemistry , Hydroxybenzoates/chemical synthesis , Phosphatidylcholines/chemistry , Phosphatidylcholines/chemical synthesisABSTRACT
The present study describes the changes in lipid profile as well as fatty acid fluxes during seed development in Jatropha curcas L. Endosperm from 34, 37, and 40 days after anthesis (DAA), incubated with [(14)C]acetate, showed significant synthesis of phosphatidylcholine (PC) at seed maturation. The fatty acid methyl ester profile showed PC from 34 DAA was rich in palmitic acid (16:0), whereas PC from 37 and 40 DAA was rich in oleic acid (18:1n-9). Molecular species analysis of diacylglycerol (DAG) indicated DAG (16:0/18:2n-6) was in abundance at 34 DAA, whereas DAG (18:1n-9/18:2n-6) was significantly high at 40 DAA. Triacylglycerol (TAG) analysis revealed TAG (16:0/18:2n-6/16:0) was abundant at 34 DAA, whereas TAG (18:1n-9/18:2n-6/18:1n-9) formed the majority at 40 DAA. Expression of two types of diacylglycerol acyltransferases varied with seed maturation. These data demonstrate stage-specific distinct pools of PC and DAG synthesis during storage TAG accumulation in Jatropha seed.
Subject(s)
Fatty Acids/analysis , Glycerophospholipids/metabolism , Jatropha/growth & development , Seeds/chemistry , Seeds/growth & development , Diglycerides/analysis , Endosperm/chemistry , Gene Expression , Oleic Acid/analysis , Palmitic Acid/analysis , Phosphatidylcholines/biosynthesis , Phosphatidylcholines/chemistry , Phosphatidylcholines/metabolism , Phospholipids/analysis , Seeds/genetics , Time Factors , Triglycerides/analysisABSTRACT
The study involved synthesis of five novel amino acid derivatives of phosphatidylethanolamine isolated from egg yolk lecithin employing a three step procedure i) N-protection of L-amino acids with BOC anhydride in alkaline medium ii) condensation of - CO2H group of N-protected amino acid with free -NH2 of PE by a peptide linkage and iii) deprotection of N-protected group of amino acids to obtain phosphatidylethanolamine-N-amino acid derivatives in 60-75% yield. The five L-amino acids used were L glycine, L-valine, L-leucine, L-isoleucine and L-phenylalanine. The amino acid derivatives were screened for anti-baterial activity against B. subtilis, S. aureus, P. aeroginosa and E. coli taking Streptomycin as reference compound and anti-fungal activity against C. albicans, S. cervisiae, A. niger taking AmphotericinB as reference compound. All the amino acid derivatives exhibited extraordinary anti-bacterial activities about 3 folds or comparable to Streptomycin and moderate or no anti-fungal activity against Amphotericin-B.
Subject(s)
Amino Acids/chemical synthesis , Amino Acids/pharmacology , Bacteria/drug effects , Fungi/drug effects , Phosphatidylethanolamines/chemistry , Phosphatidylethanolamines/isolation & purification , Drug Evaluation, Preclinical , Drug Resistance, Microbial , Egg Yolk/chemistry , Glycine/chemistry , Isoleucine/chemistry , Lecithins/chemistry , Leucine/chemistry , Phenylalanine/chemistry , Valine/chemistryABSTRACT
The synthesis of rac 1-O-alkyl-2-acetyl-sn-glycero-3-phosphocholines (6a-c), blood platelet activating ether lipid analogues has been achieved in a four-step sequence from epichlorohydrin (1). Etherification of epichlorohydrin with different alcohols namely tetradecyl (2a), hexadecyl (2b) and octadecyl (2c) alcohols gave glycidyl ethers (3a-c) with 78-80% yields. The second step involved opening of the epoxide by acetic anhydride to give acetylated products (4a-c, 76-78% yield), which were subsequently hydrolyzed selectively, a key step of the method employing a 1,3 specific lipase to obtain rac 1-O-alkyl-2- acetylglycerol (5a-c) with 45-50% yields. The hydrolyzed products (5a-c) were phosphorylated to obtain rac 1-O-alkyl-2-acetyl-sn-glycero-3-phosphocholines (6a-c) in 80-85% yields.